Win One for the Dapper

Tom Landry

Dallas Cowboys

We'll say this once (and maybe a few more times): Before the days of corporate sponsorship and space-age athletic apparel, coaches used to look like they meant business. Just look at Landry. When your fedora is placed next to your name on your team's Ring of Honor, you've probably hit on an iconic piece of style.

We appreciate Ditka's home-team enthusiasm—he still wears this get-up when the Bears are on Monday Night Football—but there are better ways of showing your pride than that sausage-casing sweater vest...

Photo: Mitchell Layton/Getty Images

Hank Stram

Dallas Texans/Kansas City Chiefs/New Orleans Saints

...like this. When modern-day coaches wear their official NFL hoodies festooned with team logos, they look like Nascar drivers. When Stram stitched one to his navy blazer, he gave Kansas City a dose of East-Coast prep.

Photo: Focus on Sport/Getty Images

Bum Phillips

Houston Oilers, New Orleans Saints

With his Texan roots and trademark Stetson, Bum Phillips was the poster child for fearless personal style. How else are you supposed to dress while coaching the Houston Oilers?

Photo: Michael Zagaris/Getty Images

Bill Belichick

Cleveland Browns, New England Patriots

Belichick's, on the other hand, is a look that shouldn't be trademarked so much as made illegal. We know you're an esoteric evil genius and all, but would it kill you to put some sleeves on those?

Photo: Elsa/Getty Images

Vince Lombardi

Green Bay Packers, Washington Redskins

Out there on The Frozen Tundra of Lambeau Field, Lombardi set the bar for cold-weather coaches: When conditions are sub-zero and you're asking your boys to grind out that last yard, you've gotta lead by example...

Photo: Vernon Biever/Getty Images

**Mike McCarthy, Mike Singletary, Wade Phillips, and Others **

...unlike these guys, who seem to run for the Antarctic-station gear every time the kickoff temp nudges fifty. It's hard to take play calls seriously when they're coming from Coach Stay Puft.

In 2006, Del Rio and Nolan petitioned the NFL to let them wear suits, leading to these custom Reebok-designed numbers. A petition to wear suits? No wonder they call it the No Fun League.

Photo: Tom Hauck/Getty Images; Doug Benc/Getty Images

John Madden

Oakland Raiders

All the king's horses and all the king's men... denied all responsibility for the Humpty-Dumpty pants John Madden wore throughout the '70s.

Photo: Focus on Sport/Getty Images

Sid Gillman

Los Angeles Rams, Los Angeles/San Diego Chargers, Houston Oilers

If NFL Films ever immortalizes you for revolutionizing the downfield passing attack, you'll wish you were sporting something as sharp as Sid's notorious bow-tied style—just check out the man's Hall of Fame bust.

Photo: Charles Aqua Viva/NFL/Getty Images

Bill Parcells

New York Giants, New England Patriots, New York Jets, Dallas Cowboys

Though he has a reputation for turning around moribund teams, The Tuna's never really fid his droopy shorts and love of elastic waistbands.

Photo: Getty Images

Mike Tomlin

Pittsburgh Steelers

And finally, probably the best-dressed coach of our times. Becoming head coach at age 34 and winning a ring at 36? That adds to the swagger. The trim warmup gear and Versace shades? That... also adds to the swagger.

Win One for the Dapper

When trying to lead a platoon of purpose-built, 300-pound athletes to gridiron glory, it's important to look the part. With the NFL season in full swing, we decided to take a look at the best- and worst-dressed coaches in pro football, past and present

We'll say this once (and maybe a few more times): Before the days of corporate sponsorship and space-age athletic apparel, coaches used to look like they meant business. Just look at Landry. When your fedora is placed next to your name on your team's Ring of Honor, you've probably hit on an iconic piece of style.